Kick back at the bar inside Vanguard (2659 S. Kinnickinnic Ave.), feast on sausages – or better yet, Durty Burgers – and watch some WWE wrestling on the telly while those “date” jitters dissipate. If things aren’t going well, you’re well positioned for a quick exit, since you paid up front at the counter.
An Artsy Day Date
You could spend hours gazing at works of visual beauty (and getting to know each other) at Milwaukee Art Museum (700 N. Art Museum Dr.), but you’ll need fuel breaks. And the museum has great ones: in the lake-facing, light-strewn lower-level restaurant, whose lunch menu is often inspired by current exhibits, and at the bar/lounge, where you can get a little sit-down-convo time over wine and cheese.
Fine Seafood and Moonlight
If you’re thinking dressy duds and glitzy environs, reserve a table at Third Coast Provisions (724 N. Milwaukee St.) and share the lobster rolls, daily whole fish preparation and (absolutely) dessert. End the night with one of the most spectacular views in the city. Take Water Street south to the Third Ward, hang a left at Pittsburgh and make a right on the KK River Trail, which you will take south a few blocks to Harbor View Park (600 S. Water St.). Enjoy the expanse of water, the Hoan Bridge and our skyline.